Oregon Vacations
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Oregon Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
The Montcler Hotel - Redberri Luxury Collection
Price was $604, price is now $500 per person
$500
per person
Dec 31 - Jan 4
found 1 day ago
Roundtrip flight included
New York (LGA) to Chicago (ORD)
Book a stay at this business-friendly hotel in Sandwich. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Farnsworth House and Silver Springs State Park are located nearby.
Hotel Riu Plaza Chicago
Downtown Chicago
Price was $1,180, price is now $809 per person
$809
per person
Dec 31 - Jan 4
found 1 day ago
Roundtrip flight included
New York (LGA) to Chicago (ORD)
Book a stay at this business-friendly hotel in Chicago. Enjoy free breakfast, free WiFi, and 2 bars/lounges. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Nice location
Reviewed on Nov 14, 2026
Eurostars Magnificent Mile
Downtown Chicago
Price was $1,094, price is now $788 per person
$788
per person
Dec 31 - Jan 4
found 1 day ago
Roundtrip flight included
New York (LGA) to Chicago (ORD)
Book a stay at this spa hotel in Chicago. Enjoy free WiFi, a full-service spa, and a fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Hotel Felix River North/Magnificent Mile
Downtown Chicago
Price was $787, price is now $626 per person
$626
per person
Dec 31 - Jan 4
found 1 day ago
Roundtrip flight included
New York (LGA) to Chicago (ORD)
Book a stay at this boutique hotel in Chicago. Enjoy breakfast (surcharge), a 24-hour health club, and valet parking (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel
Downtown Chicago
Price was $800, price is now $647 per person
$647
per person
Dec 31 - Jan 4
found 1 day ago
Roundtrip flight included
New York (LGA) to Chicago (ORD)
Book a stay at this business-friendly hotel in Chicago. Enjoy breakfast (surcharge), a 24-hour fitness center, and a 24-hour front desk. Our guests praise the helpful staff in our reviews. Popular attractions Millennium Park and Chicago Riverwalk are located nearby.
A
Reviewed on Nov 12, 2026
Sports Illustrated Resorts Chicago
Downtown Chicago
Price was $834, price is now $683 per person
$683
per person
Dec 31 - Jan 4
found 1 day ago
Roundtrip flight included
New York (LGA) to Chicago (ORD)
Book a stay at this boutique hotel in Chicago. Enjoy free WiFi, a 24-hour fitness center, and valet parking (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.
Very clean and comfortable. Valet was helpful and kind
Reviewed on Nov 13, 2026
Top Hotel Deals
Sleep Inn & Suites Oregon - Madison
1120 Park Street Oregon WI
1.68 km from city center
Book a stay at this business-friendly hotel in Oregon. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. ...
The Madison Concourse Hotel and Governor's Club
1 W Dayton St Madison WI
16.67 km from city center
Book a stay at this luxury hotel in Madison. Enjoy free WiFi, breakfast (surcharge), and a free airport shuttle. Our guests praise the breakfast and the pool ...
Motel 6 Madison, WI - East
4202 E Towne Blvd Madison WI
22.88 km from city center
Stay at this motel in Madison. Enjoy free parking, a 24-hour front desk, and daily housekeeping. Our guests praise the helpful staff and the clean rooms in our ...
Baymont by Wyndham Madison West/Middleton WI West
8102 Excelsior Dr Madison WI
20.33 km from city center
Book a stay at this family-friendly hotel in Madison. Enjoy free breakfast, free parking, and a free airport shuttle. Our guests praise the breakfast and the ...
AmericInn by Wyndham Madison West
516 Grand Canyon Dr Madison WI
17.04 km from city center
Book a stay at this business-friendly hotel in Madison. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our ...
The Edgewater
1001 Wisconsin Place Madison WI
17.02 km from city center
Book a stay at this luxury hotel in Madison. Enjoy a full-service spa, 4 bars/lounges, and breakfast (surcharge). Our guests praise the helpful staff and the ...
DoubleTree by Hilton Madison Downtown
525 West Johnson Street Madison WI
16.22 km from city center
Book a stay at this business-friendly hotel in Madison. Enjoy free WiFi, breakfast (surcharge), and a free airport shuttle. Our guests praise the helpful staff ...
DoubleTree by Hilton Madison East
4402 E Washington Ave Madison WI
23.21 km from city center
Book a stay at this business-friendly hotel in Madison. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the ...
La Quinta Inn & Suites by Wyndham Madison American Center
5217 E Terrace Dr Madison WI
25.42 km from city center
Stay at this hotel in Madison. Enjoy free breakfast, free parking, and a fitness center. Our guests praise the breakfast and the helpful staff in our reviews. ...
Tru by Hilton Madison West, WI
8102 Watts Rd. Madison WI
18.15 km from city center
Book a stay at this business-friendly hotel in Madison. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
The Dylin
611 E Dayton St Madison WI
17.14 km from city center
Stay at this aparthotel in Madison. Enjoy free WiFi, a 24-hour fitness center, and parking (surcharge). Popular attractions Camp Randall Stadium and Alliant ...
Best Western Plus InnTowner Madison
2424 University Avenue Madison WI
16.64 km from city center
Stay at this hotel in Madison. Enjoy free breakfast, free parking, and a free area shuttle. Our guests praise the breakfast and the helpful staff in our reviews. ...
Cambria Hotel Madison East
5045 Eastpark Blvd Madison WI
25.31 km from city center
Book a stay at this family-friendly hotel in Madison. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean ...
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Top Flight Deals
These prices were available within the past 7 days. Prices quoted are per person, round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.
Tue, Apr 13 - Sun, Apr 18
MSP
Minneapolis - St. Paul Intl.
MSN
Dane County Regional
$269 Roundtrip, found 3 days ago
$269
Roundtrip
found 3 days ago
Tue, Apr 13 - Sun, Apr 18
MSP
Minneapolis - St. Paul Intl.
MSN
Dane County Regional
$289 Roundtrip, found 3 days ago
$289
Roundtrip
found 3 days ago
Tue, Apr 13 - Sun, Apr 18
MSP
Minneapolis - St. Paul Intl.
MSN
Dane County Regional
$339 Roundtrip, found 3 days ago
$339
Roundtrip
found 3 days ago
Tue, Nov 17 - Sun, Dec 6
LAS
Harry Reid Intl.
MSN
Dane County Regional
$684 Roundtrip, found 2 days ago
$684
Roundtrip
found 2 days ago